data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;A Sequential Enantioselective, Organocatalytic Route to Chiral 1,2-Oxazines and Chiral Pyridazines ; _publ_contact_author_name 'Prof. Steven V. Ley' _publ_contact_author_email SVL1000@CAM.AC.UK loop_ _publ_author_name S.Ley 'Sirirat Kumarn' 'Deborah A. Longbottom' 'Alexander J. Oelke' 'David M. Shaw' # Attachment 'sl0641.cif' data_sl0641 _database_code_depnum_ccdc_archive 'CCDC 649830' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N3 O2' _chemical_formula_sum 'C15 H17 N3 O2' _chemical_formula_weight 271.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6411(3) _cell_length_b 8.4172(3) _cell_length_c 12.5210(5) _cell_angle_alpha 71.4020(10) _cell_angle_beta 85.487(2) _cell_angle_gamma 63.189(2) _cell_volume 679.18(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8155 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 29.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; No unusual features. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7896 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 29.10 _reflns_number_total 3607 _reflns_number_gt 2751 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.1596P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3607 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.75130(13) 0.47485(13) 0.08842(8) 0.0359(2) Uani 1 1 d . . . O2 O 0.69634(13) 0.83353(13) 0.31271(8) 0.0370(2) Uani 1 1 d . . . N1 N 0.49096(15) 0.72460(14) 0.12719(9) 0.0275(2) Uani 1 1 d . . . N2 N 0.48250(14) 0.84590(14) 0.18607(9) 0.0286(2) Uani 1 1 d . . . N3 N 0.78047(14) 0.61265(14) 0.21737(9) 0.0284(2) Uani 1 1 d . . . C1 C 0.38353(18) 0.82085(18) 0.01473(11) 0.0305(3) Uani 1 1 d . . . H1A H 0.3346 0.7407 -0.0030 0.037 Uiso 1 1 calc R . . H1B H 0.4737 0.8420 -0.0431 0.037 Uiso 1 1 calc R . . C2 C 0.21381(19) 1.00527(18) 0.01114(12) 0.0334(3) Uani 1 1 d . . . H2 H 0.1325 1.0778 -0.0574 0.040 Uiso 1 1 calc R . . C3 C 0.16836(18) 1.07500(18) 0.09605(11) 0.0330(3) Uani 1 1 d . . . H3 H 0.0571 1.1933 0.0858 0.040 Uiso 1 1 calc R . . C4 C 0.28725(17) 0.97288(17) 0.20840(11) 0.0289(3) Uani 1 1 d . . . H4 H 0.3003 1.0670 0.2355 0.035 Uiso 1 1 calc R . . C5 C 0.18870(19) 0.87297(19) 0.29864(11) 0.0339(3) Uani 1 1 d . . . H5 H 0.1647 0.7870 0.2688 0.041 Uiso 1 1 calc R . . C6 C -0.0096(2) 1.0178(2) 0.32053(14) 0.0465(4) Uani 1 1 d . . . H6A H -0.0724 0.9534 0.3770 0.070 Uiso 1 1 calc R . . H6B H -0.0943 1.0880 0.2500 0.070 Uiso 1 1 calc R . . H6C H 0.0109 1.1047 0.3486 0.070 Uiso 1 1 calc R . . C7 C 0.3186(2) 0.7563(3) 0.40859(14) 0.0548(4) Uani 1 1 d . . . H7A H 0.2491 0.6995 0.4647 0.082 Uiso 1 1 calc R . . H7B H 0.3497 0.8372 0.4370 0.082 Uiso 1 1 calc R . . H7C H 0.4407 0.6571 0.3949 0.082 Uiso 1 1 calc R . . C8 C 0.68354(17) 0.58953(17) 0.13863(10) 0.0278(3) Uani 1 1 d . . . C9 C 0.65536(18) 0.77318(17) 0.24750(11) 0.0285(3) Uani 1 1 d . . . C10 C 0.98658(17) 0.50772(17) 0.25270(11) 0.0276(3) Uani 1 1 d . . . C11 C 1.04510(19) 0.42782(19) 0.36702(11) 0.0341(3) Uani 1 1 d . . . H11 H 0.9498 0.4398 0.4213 0.041 Uiso 1 1 calc R . . C12 C 1.2440(2) 0.3302(2) 0.40157(12) 0.0405(3) Uani 1 1 d . . . H12 H 1.2855 0.2741 0.4798 0.049 Uiso 1 1 calc R . . C13 C 1.38264(19) 0.3144(2) 0.32199(13) 0.0390(3) Uani 1 1 d . . . H13 H 1.5189 0.2477 0.3457 0.047 Uiso 1 1 calc R . . C14 C 1.32244(19) 0.39560(19) 0.20822(12) 0.0345(3) Uani 1 1 d . . . H14 H 1.4178 0.3853 0.1540 0.041 Uiso 1 1 calc R . . C15 C 1.12383(18) 0.49221(17) 0.17232(11) 0.0301(3) Uani 1 1 d . . . H15 H 1.0826 0.5468 0.0940 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0337(5) 0.0352(5) 0.0381(5) -0.0188(4) 0.0011(4) -0.0099(4) O2 0.0345(5) 0.0419(5) 0.0407(5) -0.0215(4) -0.0006(4) -0.0162(4) N1 0.0274(5) 0.0285(5) 0.0282(5) -0.0123(4) 0.0007(4) -0.0114(4) N2 0.0259(5) 0.0300(5) 0.0326(6) -0.0151(4) 0.0017(4) -0.0112(4) N3 0.0250(5) 0.0300(5) 0.0300(6) -0.0123(4) 0.0006(4) -0.0101(4) C1 0.0299(6) 0.0340(6) 0.0283(6) -0.0104(5) -0.0010(5) -0.0143(5) C2 0.0293(6) 0.0342(7) 0.0328(7) -0.0055(5) -0.0013(5) -0.0139(5) C3 0.0268(6) 0.0292(6) 0.0375(7) -0.0077(5) 0.0007(5) -0.0097(5) C4 0.0251(6) 0.0272(6) 0.0349(7) -0.0124(5) 0.0043(5) -0.0110(5) C5 0.0332(7) 0.0361(7) 0.0375(7) -0.0139(6) 0.0070(5) -0.0191(6) C6 0.0386(8) 0.0520(9) 0.0546(10) -0.0243(8) 0.0181(7) -0.0225(7) C7 0.0484(9) 0.0659(11) 0.0392(9) 0.0020(8) 0.0025(7) -0.0292(8) C8 0.0269(6) 0.0283(6) 0.0282(6) -0.0094(5) 0.0020(5) -0.0122(5) C9 0.0271(6) 0.0305(6) 0.0293(6) -0.0108(5) 0.0029(5) -0.0134(5) C10 0.0248(6) 0.0273(6) 0.0301(6) -0.0094(5) 0.0004(5) -0.0107(5) C11 0.0317(6) 0.0405(7) 0.0291(7) -0.0105(6) 0.0026(5) -0.0158(6) C12 0.0370(7) 0.0456(8) 0.0334(7) -0.0099(6) -0.0071(6) -0.0144(6) C13 0.0266(6) 0.0411(7) 0.0485(9) -0.0191(7) -0.0038(6) -0.0105(6) C14 0.0293(6) 0.0370(7) 0.0423(8) -0.0195(6) 0.0080(5) -0.0154(6) C15 0.0319(6) 0.0293(6) 0.0288(6) -0.0099(5) 0.0034(5) -0.0134(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.2166(14) . ? O2 C9 1.2129(15) . ? N1 C8 1.3779(15) . ? N1 N2 1.4153(13) . ? N1 C1 1.4722(16) . ? N2 C9 1.3569(16) . ? N2 C4 1.4605(15) . ? N3 C8 1.3877(15) . ? N3 C9 1.4089(15) . ? N3 C10 1.4359(15) . ? C1 C2 1.4973(18) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.3234(19) . ? C2 H2 0.9500 . ? C3 C4 1.5062(18) . ? C3 H3 0.9500 . ? C4 C5 1.5434(18) . ? C4 H4 1.0000 . ? C5 C7 1.523(2) . ? C5 C6 1.5290(19) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C11 1.3844(17) . ? C10 C15 1.3871(17) . ? C11 C12 1.3868(18) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.381(2) . ? C13 H13 0.9500 . ? C14 C15 1.3883(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 N2 107.17(9) . . ? C8 N1 C1 119.43(10) . . ? N2 N1 C1 114.62(9) . . ? C9 N2 N1 110.17(9) . . ? C9 N2 C4 127.80(10) . . ? N1 N2 C4 116.74(9) . . ? C8 N3 C9 110.68(10) . . ? C8 N3 C10 126.01(10) . . ? C9 N3 C10 122.72(10) . . ? N1 C1 C2 110.58(10) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C3 C2 C1 125.04(12) . . ? C3 C2 H2 117.5 . . ? C1 C2 H2 117.5 . . ? C2 C3 C4 122.13(12) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? N2 C4 C3 106.00(10) . . ? N2 C4 C5 113.65(10) . . ? C3 C4 C5 112.40(10) . . ? N2 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C5 C4 H4 108.2 . . ? C7 C5 C6 110.10(12) . . ? C7 C5 C4 111.85(11) . . ? C6 C5 C4 109.84(11) . . ? C7 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C4 C5 H5 108.3 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 N1 125.78(11) . . ? O1 C8 N3 128.04(11) . . ? N1 C8 N3 106.19(10) . . ? O2 C9 N2 128.12(11) . . ? O2 C9 N3 126.97(12) . . ? N2 C9 N3 104.90(10) . . ? C11 C10 C15 121.01(11) . . ? C11 C10 N3 119.22(11) . . ? C15 C10 N3 119.74(11) . . ? C10 C11 C12 119.43(12) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C13 120.08(13) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 119.95(12) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.63(12) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 118.89(12) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 -9.59(13) . . . . ? C1 N1 N2 C9 -144.59(11) . . . . ? C8 N1 N2 C4 -165.97(10) . . . . ? C1 N1 N2 C4 59.03(13) . . . . ? C8 N1 C1 C2 -158.07(11) . . . . ? N2 N1 C1 C2 -28.93(14) . . . . ? N1 C1 C2 C3 1.43(19) . . . . ? C1 C2 C3 C4 0.3(2) . . . . ? C9 N2 C4 C3 155.77(12) . . . . ? N1 N2 C4 C3 -52.65(13) . . . . ? C9 N2 C4 C5 -80.27(15) . . . . ? N1 N2 C4 C5 71.30(14) . . . . ? C2 C3 C4 N2 23.19(16) . . . . ? C2 C3 C4 C5 -101.54(14) . . . . ? N2 C4 C5 C7 54.56(15) . . . . ? C3 C4 C5 C7 174.97(12) . . . . ? N2 C4 C5 C6 177.13(11) . . . . ? C3 C4 C5 C6 -62.46(14) . . . . ? N2 N1 C8 O1 -170.71(12) . . . . ? C1 N1 C8 O1 -38.27(18) . . . . ? N2 N1 C8 N3 9.13(13) . . . . ? C1 N1 C8 N3 141.57(11) . . . . ? C9 N3 C8 O1 173.97(13) . . . . ? C10 N3 C8 O1 2.6(2) . . . . ? C9 N3 C8 N1 -5.86(14) . . . . ? C10 N3 C8 N1 -177.23(11) . . . . ? N1 N2 C9 O2 -175.45(13) . . . . ? C4 N2 C9 O2 -22.4(2) . . . . ? N1 N2 C9 N3 5.78(13) . . . . ? C4 N2 C9 N3 158.85(11) . . . . ? C8 N3 C9 O2 -178.75(13) . . . . ? C10 N3 C9 O2 -7.1(2) . . . . ? C8 N3 C9 N2 0.04(14) . . . . ? C10 N3 C9 N2 171.74(11) . . . . ? C8 N3 C10 C11 -129.91(14) . . . . ? C9 N3 C10 C11 59.70(16) . . . . ? C8 N3 C10 C15 51.86(17) . . . . ? C9 N3 C10 C15 -118.52(13) . . . . ? C15 C10 C11 C12 -0.2(2) . . . . ? N3 C10 C11 C12 -178.45(12) . . . . ? C10 C11 C12 C13 0.5(2) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C15 -0.5(2) . . . . ? C11 C10 C15 C14 -0.36(18) . . . . ? N3 C10 C15 C14 177.83(11) . . . . ? C13 C14 C15 C10 0.74(19) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.205 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.044